167

Recently Sold Sugarloaf, FL Homes

Section Image
  • /2

    $1,030,000

    Sold Nov 19, 2025

    22521 Jolly Roger Dr, Cudjoe Key, FL 33042

    • 4 Beds
    • 2.5 Baths
    • 1,728 Sq Ft
    • Built 2010

    Last Sold Summary

    • $596/SF
    • 0 Days On Market

    Current Estimated Value $1,108,949

    Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

    22521 Jolly Roger Dr, Cudjoe Key, FL 33042
  • /56

    $1,725,000

    Sold Jul 11, 2025

    17159 Amberjack Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft
    • Built 1989

    Last Sold Summary

    • 14% Below List Price
    • $1,039/SF
    • 258 Days On Market

    Current Estimated Value $1,733,649

    Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

    17159 Amberjack Ln, Summerland Key, FL 33042
  • /33

    $910,000

    Sold Apr 13, 2026

    151 Cutthroat Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2.5 Baths
    • 1,140 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $798/SF
    • 46 Days On Market

    Current Estimated Value $915,727

    Last Listing Agent Heather Bennett Florida Keys Real Estate Co. (KW)

    151 Cutthroat Dr, Summerland Key, FL 33042
  • /45

    $630,000

    Sold Dec 08, 2025

    22970 Sharp Ln, Summerland Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 576 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Below List Price
    • $1,094/SF
    • 4 Days On Market

    Current Estimated Value $664,476

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    22970 Sharp Ln, Summerland Key, FL 33042
  • /37

    $268,000

    Sold Apr 27, 2026

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042

    • Land
    • 2,178 Sq Ft
    • $5,360,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 52 Days On Market

    Current Estimated Value $285,512

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
  • /6

    $1,937,500

    Sold Jun 05, 2026

    1058 Buttonwood Dr E, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,767 Sq Ft
    • Built 2001

    Last Sold Summary

    • $1,096/SF
    • 0 Days On Market

    Current Estimated Value $1,592,238

    Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

    1058 Buttonwood Dr E, Summerland Key, FL 33042
  • /125

    $5,000,000

    Sold Jun 18, 2026

    24200 Overseas Hwy, Summerland Key, FL 33042

    • 5 Beds
    • 5.5 Baths
    • 3,000 Sq Ft
    • Built 1977

    Last Sold Summary

    • 19% Below List Price
    • $1,667/SF
    • 106 Days On Market

    Current Estimated Value $5,281,295

    Last Listing Agent Sylvia Werling Keller Williams Key West Compass Realty

    24200 Overseas Hwy, Summerland Key, FL 33042
  • /5

    $725,000

    Sold Jul 30, 2025

    19462 Canal Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,394 Sq Ft
    • Built 1990

    Last Sold Summary

    • 6% Below List Price
    • $520/SF
    • 3 Days On Market

    Current Estimated Value $748,620

    Last Listing Agent Jacqui Norman Berkshire Hathaway HomeServices Knight & Gardner Realty

    19462 Canal Dr, Summerland Key, FL 33042
  • /2

    $55,000

    Sold Oct 22, 2025

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042

    • Land
    • 5,000 Sq Ft
    • $479,160 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 2 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042
  • /49

    $280,000

    Sold Jun 03, 2026

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft
    • Built 1976

    Last Sold Summary

    • $406/SF
    • 98 Days On Market

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
  • /68

    $2,250,000

    Sold Apr 03, 2026

    24266 Caribbean Dr W, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,055 Sq Ft
    • Built 1981

    Last Sold Summary

    • 2% Below List Price
    • $1,095/SF
    • 14 Days On Market

    Current Estimated Value $2,231,985

    Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

    24266 Caribbean Dr W, Summerland Key, FL 33042
  • /41

    $775,000

    Sold May 01, 2026

    22939 Privateer Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 1988

    Last Sold Summary

    • $602/SF
    • 3 Days On Market

    Current Estimated Value $769,267

    Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

    22939 Privateer Dr, Summerland Key, FL 33042
  • /67

    $3,150,000

    Sold Jun 09, 2026

    270 E Caribbean Dr, Summerland Key, FL 33042

    • 4 Beds
    • 4 Baths
    • 2,375 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $1,326/SF
    • 22 Days On Market

    Current Estimated Value $2,722,116

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    270 E Caribbean Dr, Summerland Key, FL 33042
  • /38

    $4,275,000

    Sold Mar 04, 2026

    231 E Shore Dr Unit 7, Key West, FL 33040

    • 5 Beds
    • 5.5 Baths
    • 4,103 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $1,042/SF
    • 173 Days On Market

    Last Listing Agent Stephanie Marinucci Serhant

    231 E Shore Dr Unit 7, Key West, FL 33040
  • /34

    $600,000

    Sold Sep 22, 2025

    19557 Mayan St, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 989 Sq Ft
    • Built 1958

    Last Sold Summary

    • 5% Below List Price
    • $607/SF
    • 186 Days On Market

    Current Estimated Value $643,990

    Last Listing Agent Lola McKee eXp Realty LLC

    19557 Mayan St, Summerland Key, FL 33042
  • /71

    $3,150,000

    Sold Aug 28, 2025

    225 Colson Dr, Summerland Key, FL 33042

    • 6 Beds
    • 6.5 Baths
    • 4,976 Sq Ft
    • Built 2010

    Last Sold Summary

    • 10% Below List Price
    • $633/SF
    • 118 Days On Market

    Current Estimated Value $3,360,263

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    225 Colson Dr, Summerland Key, FL 33042
  • /20

    $207,000

    Sold Apr 09, 2026

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

    • Land
    • 1,742 Sq Ft
    • $5,175,000 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 375 Days On Market

    Current Estimated Value $247,743

    Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
  • /24

    $310,000

    Sold Apr 16, 2026

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

    • Land
    • 2,178 Sq Ft
    • $6,200,000 per Acre

    Last Sold Summary

    • 19% Below List Price
    • 118 Days On Market

    Current Estimated Value $317,747

    Last Listing Agent Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
  • /54

    $1,550,000

    Sold Nov 05, 2025

    15 Bay Dr, Key West, FL 33040

    • 3 Beds
    • 2 Baths
    • 2,028 Sq Ft
    • Built 1990

    Last Sold Summary

    • 18% Below List Price
    • $764/SF
    • 248 Days On Market

    Current Estimated Value $1,594,959

    Last Listing Agent Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

    15 Bay Dr, Key West, FL 33040
  • /35

    $817,500

    Sold Dec 01, 2025

    22878 Privateer Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 948 Sq Ft
    • Built 1989

    Last Sold Summary

    • 7% Below List Price
    • $862/SF
    • 133 Days On Market

    Current Estimated Value $825,324

    Last Listing Agent Pamela Stangler Expert Realty LLC

    22878 Privateer Dr, Summerland Key, FL 33042
  • /83

    $3,300,000

    Sold Jul 11, 2025

    16705 Tamarind Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 3,086 Sq Ft
    • Built 2015

    Last Sold Summary

    • 27% Below List Price
    • $1,069/SF
    • 299 Days On Market

    Current Estimated Value $3,306,557

    Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

    16705 Tamarind Rd, Summerland Key, FL 33042
  • /3

    $75,000

    Sold Oct 10, 2025

    0 Asturias Rd, Cudjoe Key, FL 33042

    • Land
    • 1.01 Acres
    • $74,124 per Acre

    Last Sold Summary

    • 62% Below List Price
    • 41 Days On Market

    Last Listing Agent Maryann Warren Coldwell Banker - Ft. Lauderdale

    0 Asturias Rd, Cudjoe Key, FL 33042
  • /2

    $600,000

    Sold Jul 14, 2025

    701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft
    • Built 1993

    Last Sold Summary

    • 14% Below List Price
    • $735/SF
    • 56 Days On Market

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042
  • /2

    $49,000

    Sold Oct 03, 2025

    Lot 24 Rainbow Beach, Big Torch Key, FL 33042

    • Land
    • 5,499 Sq Ft
    • $388,080 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 50 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 24 Rainbow Beach, Big Torch Key, FL 33042
  • /61

    $2,675,000

    Sold Jun 01, 2026

    20844 4th Ave W, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,951 Sq Ft
    • Built 1997

    Last Sold Summary

    • 4% Below List Price
    • $906/SF
    • 10 Days On Market

    Current Estimated Value $2,729,849

    Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    20844 4th Ave W, Summerland Key, FL 33042
  • /75

    $830,000

    Sold Sep 15, 2025

    22738 Blackbeard Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1989

    Last Sold Summary

    • 17% Below List Price
    • $692/SF
    • 84 Days On Market

    Current Estimated Value $877,453

    Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

    22738 Blackbeard Ln, Summerland Key, FL 33042
  • /41

    $1,105,000

    Sold Sep 26, 2025

    22946 Bluegill Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1975

    Last Sold Summary

    • 14% Below List Price
    • $921/SF
    • 255 Days On Market

    Current Estimated Value $1,130,346

    Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt RE Co.

    22946 Bluegill Ln, Summerland Key, FL 33042
  • /47

    $1,075,000

    Sold May 13, 2026

    110 Doubloon Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Below List Price
    • $853/SF
    • 9 Days On Market

    Current Estimated Value $1,120,391

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    110 Doubloon Ln, Summerland Key, FL 33042
  • /11

    $560,000

    Sold Jun 18, 2026

    22963 Anne Bonny Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 834 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $671/SF
    • 43 Days On Market

    Current Estimated Value $584,856

    Last Listing Agent Judith Exposito Luxe Properties

    22963 Anne Bonny Ln, Summerland Key, FL 33042
  • /44

    $810,000

    Sold Feb 19, 2026

    57 Palm Dr, Key West, FL 33040

    • 3 Beds
    • 3 Baths
    • 1,380 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $587/SF
    • 185 Days On Market

    Current Estimated Value $821,991

    Last Listing Agent Suzanne Moore Suzanne Moore Real Estate

    57 Palm Dr, Key West, FL 33040
  • /34

    $840,207

    Sold Jul 03, 2026

    131 Doubloon Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1999

    Last Sold Summary

    • 14% Below List Price
    • $577/SF
    • 61 Days On Market

    Current Estimated Value $981,778

    Last Listing Agent Jenifer Hirsch Bluescape Real Estate

    131 Doubloon Ln, Summerland Key, FL 33042
  • /5

    $75,000

    Sold Jun 22, 2026

    Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

    • Land
    • 14,810 Sq Ft
    • $220,588 per Acre

    Last Sold Summary

    • 46% Below List Price
    • 177 Days On Market

    Last Listing Agent Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

    Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
  • /8

    $340,000

    Sold Dec 11, 2025

    0 Overseas Hwy, Summerland Key, FL 33042

    • Land
    • 12,500 Sq Ft
    • $1,184,832 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 328 Days On Market

    Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

    0 Overseas Hwy, Summerland Key, FL 33042
  • /14

    $205,000

    Sold May 20, 2026

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042

    • Land
    • 1,742 Sq Ft
    • $5,125,000 per Acre

    Last Sold Summary

    • 21% Below List Price
    • 56 Days On Market

    Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
  • /43

    $1,700,000

    Sold Jan 30, 2026

    22562 Jolly Roger Dr, Summerland Key, FL 33042

    • 4 Beds
    • 2 Baths
    • 2,074 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Below List Price
    • $820/SF
    • 140 Days On Market

    Current Estimated Value $1,708,368

    Last Listing Agent Krystal Thomas eXp Realty LLC

    22562 Jolly Roger Dr, Summerland Key, FL 33042
  • /57

    $2,800,000

    Sold Oct 30, 2025

    22967 Redfish Ln, Cudjoe Key, FL 33042

    • 3 Beds
    • 3.5 Baths
    • 3,747 Sq Ft
    • Built 2019

    Last Sold Summary

    • 7% Below List Price
    • $747/SF
    • 37 Days On Market

    Current Estimated Value $2,851,119

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    22967 Redfish Ln, Cudjoe Key, FL 33042
  • /44

    $700,000

    Sold Jan 09, 2026

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $810/SF
    • 23 Days On Market

    Last Listing Agent Holly Burger RE/MAX Keys Connection (KW)

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
  • /8

    $199,000

    Sold Jul 22, 2025

    13 Beach Dr, Key West, FL 33040

    • Land
    • 4,133 Sq Ft
    • $2,097,372 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 149 Days On Market

    Current Estimated Value $200,387

    Last Listing Agent Natallie Liz Expert Realty LLC (HQ)

    13 Beach Dr, Key West, FL 33040
  • /48

    $291,000

    Sold Mar 03, 2026

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1985

    Last Sold Summary

    • 9% Below List Price
    • $404/SF
    • 133 Days On Market

    Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
  • /43

    $1,410,000

    Sold Apr 30, 2026

    17152 Marlin Dr, Sugarloaf Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1989

    Last Sold Summary

    • 12% Below List Price
    • $1,175/SF
    • 70 Days On Market

    Current Estimated Value $1,465,842

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17152 Marlin Dr, Sugarloaf Key, FL 33042

Showing Results 1 - 40, Page 1 of 5

How to Buy a Home How to Finance a Home How to Sell a Home